Aromatic amine derivative and organic electroluminescent element comprising the same
a technology of organic electroluminescent elements and amine derivatives, which is applied in the direction of thermoelectric devices, discharge tube luminescnet screens, natural mineral layered products, etc., can solve the problems of poor luminous efficiency, low luminance, and inability to achieve practical application, so as to and improve the luminous efficiency and luminous lifetime of organic el devices.
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synthesis example 1
Synthesis of Compound (D-1)
[0129]Compound (D-1) was synthesized by the following steps.
[0130]
Synthesis Example (1-1)
Synthesis of Intermediate 1
[0131]In an argon stream, 1000 mL-recovery flask was charged with 27.5 g of 1-bromo-4-(trimethylsilyl)benzene, 33.5 g of aniline, 1.65 g of tris(dibenzylideneacetone)dipalladium (0), 2.24 g of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 23.0 g of sodium tert-butoxide and toluene. The resultant was allowed to react at 100° C. for 6 hours.
[0132]After cooling, the reaction solution was filtered through Celite, and the filtrate was concentrated. The concentrated filtrate was purified by silica gel chromatography (toluene / hexane (15 / 85)), and dried under reduced pressure, whereby 23.1 g of colorless, transparent liquid was obtained. As a result of the measurement by FD-MS (field desorption mass spectrometry), the compound was confirmed to be intermediate 1.
Synthesis Example (1-2)
Synthesis of Intermediate 2
synthesis example 2
Synthesis of Compound (D-3)
[0141]Compound (D-3) was synthesized according to the following steps.
[0142]
Synthesis Example (2-1)
Synthesis of Intermediate 4
[0143]Synthesis was conducted in the same manner as in Synthesis Example (1-1): Synthesis of Intermediate 1, except that 4-bromobenzyl bromide was used instead of 1-bromo-4-(trimethylsilyl)benzene and 3,5-dimethyldiphenylamine was used instead of aniline. As a result of the measurement by FD-MS (field desorption mass spectrometry), the compound was confirmed to be intermediate 4.
Synthesis Example (2-2)
Synthesis of Intermediate 5
[0144]In an argon stream, a 300 mL-recovery flask was charged with 9.80 g of the intermediate 4 and 7.10 g of triethyl phosphite, and the resultant was heated, and generated ethyl bromide was removed by distillation. Thereafter, triethyl phosphite remained unreacted was removed by distillation under reduced pressure, whereby 10.8 g of white solids were obtained. As a result of the measurement by FD-MS (field ...
synthesis example 3
Synthesis of Compound (D-11)
[0149]Compound D-11 was synthesized by the following steps.
[0150]
Synthesis Example (3-1)
Synthesis of Intermediate 7
[0151]In an argon stream, a 500 mL-recovery flask was charged with 14.2 g of 6-bromo-2-naphthyl trifluoromethanesulfonate, 6.9 g of 4-chlorophenylboronic acid, 1.4 g of tetraxis(triphenylphosphine)palladium (0), 12.8 g (clean water 60 mL) of sodium carbonate and toluene. In an argon stream, the resultant was allowed to react with reflux for 8 hours.
[0152]Separation was conducted by adding clean water and toluene. After extracting an aqueous phase with toluene, the organic phase thus obtained was washed with clean water and saturated saline, dried with sodium sulfate, and a crude product thus obtained was purified by silica gel chromatography (toluene / hexane (30 / 70)). The resultant solids were dried under reduced pressure, whereby 8.6 g of white solids were obtained. As a result of the measurement by FD-MS (field desorption mass spectrometry),...
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